
About Us
Apella’s Southold team offers an extensive range of planning and investment management services for every type of investor, from high-net worth families with complex tax management and estate planning needs to the young professional just starting to plan their financial future. No matter what type of planning assistance you require, we’ll create a customized, comprehensive wealth management plan designed around your unique goals.
Our advice is objective, and our investment management strategies translate cutting-edge academic research into sophisticated portfolios that are focused on helping all clients achieve their personal goals. Wee seek to build tight knit, long-term relationships based on trust, and work closely together to help you make informed decisions that will keep you on track for the long term.
We’ll help you anticipate and prepare for life’s biggest financial hurdles, so you can worry less about the future and focus more on enjoying today. Whether it’s determining the best college savings approach for you and your family, developing a strategy to maximize your income in retirement, or establishing a legacy for future generations, we’ll develop a road map designed to get you where you want to go.
Our clients have access to a team of professionals and specialists who are dedicated to helping you achieve what matters to you most. We’re committed to putting our collective knowledge and experience to work on your behalf.
Our Services
- Comprehensive financial planning
- Making sure your portfolio supports your long-term goals through investment management
- Protecting your family, yourself, your assets and your business through insurance
- Helping families plan and prepare for educating children and grandchildren
- Helping business owners protect their business, provide benefits to employees, or buy or sell a business
- Making sure you have money to pay for the unexpected as well as a regular income in retirement through cash and income planning
- Helping you leave a legacy for your loved ones and your preferred charities through estate planning
- Working closely with your other financial professionals, including your CPA and Estate Attorney, to ensure an efficient and coordinated approach
Special Focus
- Tax Management and Tax Efficiency
- Retirement Income Planning
- High-Net Worth Solutions
Resources
The Apella Difference
We start with your life–and build your plan around it. We are passionate about working with our clients and helping them achieve their most important long-term goals
The Client Journey
Helping you get from today to some day. Our advisory process starts with where you are today–both personally and financially–and where you want to go.
Meet Jason Gentile
Jason fell in love with the advisory business while he was still in college, and after an internship was offered a full-time position with a financial firm even before he graduated.
Jason Gentile, CFP®
Shawn O'Sullivan, CFP®
Shawn O’Sullivan, CFP®, has been helping clients plan for and achieve their long term financial goals for more than a decade. As a Financial Planner and Senior Wealth Advisor at Apella, Shawn believes that thoughtful financial planning is the cornerstone of any successful investment strategy. He is dedicated to providing clients with the structure, guidance, and confidence needed to navigate the complexities of investing and pursue their goals with clarity and purpose.
In addition to his advisory role, Shawn serves on the firm’s Investment Committee, where he helps guide the evolution of Apella's investment strategies and offerings.
Before working as a full time advisor, Shawn gained extensive experience in operations and portfolio management and played a key role in building the foundation of Apella’s trading and research teams. This experience continues to inform his disciplined, analytical approach to financial planning and investment management.
Shawn is a Certified Financial Planner™ professional. He earned his degree in Economics from the University of Connecticut and completed his financial planning education and capstone program through Bryant University.
Shawn O'Sullivan, CFP®
As Manager of Financial Planning, Matt leads Apella’s team of paraplanners to assist financial advisors in creating thorough, comprehensive financial plans. Matt is also responsible for maintaining efficient planning processes, integrating new planning technologies into existing technology stack, and serves as a resource for advanced case consultation. Matt initially joined Apella Wealth in 2019 as a Portfolio Analyst and Paraplanner. Prior to Apella, he worked at Northwestern Mutual as a financial advisor specializing in life and disability insurance from 2017-2019.
Support Team
Alexandra O'Sullivan
Alexandra Coady works as a client relationship specialist for Jason Gentiles team. She is a recent graduate of Central Connecticut State University where she obtained a degree in Biochemistry. Prior to joining the Apella team in 2023, Alex was employed by RBC Wealth management. In her spare time, she enjoys spending time with friends and family, reading, and going to the beach.
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